Can Federer win? Will Serena break her slump? The 9 biggest questions for Wimbledon 2014

The Wimbledon draws were unveiled Friday afternoon in London, days before the 2014 championship kicks off with reigning men’s champion Andy Murray taking to Centre Court on Monday afternoon. Ahead of the hotly-anticipated grass-court event, For The Win looks at nine burning questions about Wimbledon 2014.

1. Who got the toughest draw to the semifinals: Djokovic, Nadal, Murray or Federer?

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When the men’s draw is released, the first anyone does is look ahead to the potential semifinals. This time around it’s Djokovic vs. Murray and Federer vs Nadal. But what about the paths to get there?

Nadal’s path is the toughest, especially consider we have to look at his earlier draw, as he’s only won one match at Wimbledon in his past two appearances. The nine-time French Open champion opens against Marin Klizan, a far more dangerous opponent than either of Nadal’s other recent Wimbledon vanquishers. Nadal could then face one of said vanquishers, Lukas Rosol, in the second round. If it’s not Rosol in the second, it’d be up-and-coming Frenchman Benoit Paire. Then, a looming third-rounder with the big-serving Ivo Karlovic. Nadal and Serena Williams can commiserate. Their draws are rough.

Murray may have the easiest path to the semis (though a potential quarterfinal with Grigor Dimitrov would be fun to watch). But that won’t be of any consolation if he runs into Novak Djokovic in the semis. Speaking of Djokovic, he got the short end by drawing Berdych for his quarter, but that won’t cause him too much angst. We’ll get to Federer’s draw in a bit.

2. How bummed is Maria Sharapova about being placed in Serena Williams’ quarter?

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Once again, Serena Williams and Maria Sharapova are in the same quarter, setting a possible showdown in the round of eight. Is this bad for Sharapova? Probably, but it didn’t work out too poorly for her at the French Open, did it? Maybe the draw opens up for Masha like it did at Roland Garros. Or maybe she, gasp, breaks the streak and gets the best of Serena?

Look, it’s going to happen one day. This 10-year drought can’t last forever. Sharapova is too good to let it happen. But it might take something Sharapova isn’t great at: Getting out to a fast start. Sharapova is the ultimate grinder. She’s won seven matches since April after dropping the first set, including three at the French Open. But in her last 10 matches against Serena, Sharapova has dropped the first set nine times by scores of 6-1, 6-1, 6-0, 6-4, 6-3, 6-1, 6-4, 6-2 and 6-4. In those matches, she’s never forced a third. You can’t afford to get into an early hole when you’ve lost 15 straight matches over 10 years to your biggest rival. For Sharapova, winning the first is the confidence boost she needs.

3. Is this the time for Roger Federer?

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When discussing whether Roger Federer has another major in him, this is the usual refrain: He can win a Slam, but his draw has to open up. Though the early buzz on Federer’s Wimbledon path is that it’s tough, I see a path that could be vastly different than it looks today. Jerzey Janowicz looms as a tough fourth-rounder, but he’s the men’s version of Sabine Lisicki, struggling since making a Wimbledon star turn in 2013. (Janowicz is 17-21 since.) Another potential fourth-round opponent is John Isner, whose never made it out of the second round at Wimbledon. Wawrinka, the quarterfinal draw, is 1-4 at Wimbledon this decade. And as for a potential semifinal against Nadal, we all know about Rafa’s recent grass-court woes.

4. Just how brutal is Serena Williams’ draw?

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It’s bad. As I wrote in a post earlier today about Serena’s Centre Court snub, you literally couldn’t have drawn up a harder one. Serena faces the hardest seed in each possible section of her half of the draw (Alize Cornet, Eugenie Bouchard/Andrea Petkovic, Maria Sharapova, Simona Halep). Now that there’s a book on how to beat her (hit it deep and keep her in the center of the court), playing against high-quality opponents only becomes more dangerous. Serena is still the overwhelming favorite (3/2 to win at most oddsmakers) but that draw won’t make a sixth title easy.

But don’t cry too much for Serena. You know who has a tougher draw than her? The two women who might have to play her in the fourth round, Eugenie Bouchard and Andrea Petkovic. However frustrated Serena might be, multiply that by 10 for Bouchard and Petkovic.

5. Who else had bad draw luck?

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Poor Ryan Harrison. When you’re No. 140 in the world, you shouldn’t expect any breaks. But, man, Harrison can’t even sniff one. The 22-year-old American, who was once as high as No. 43 in the rankings, faces No. 11 Grigor Dimitrov in the first round. It continues a long run of difficult draws for the would-be American star. Here’s who Harrison has lost to in every Grand Slam since the start of 2012: Gael Monfils, Rafael Nadal, No. 25 Jeremy Chardy, John Isner (second round), Novak Djokovic (second round), Juan Martin Del Potro (second round), Novak Djokovic (second round), No. 12 Gilles Simon, Andy Murray. The odds of pulling those draws at 10 consecutive Slams is probably equivalent to getting a perfect NCAA bracket. What’s it going to take for Harrison to catch a qualifier in the first and a middling talent in the second?

6. Which players outside the top 10 could make a deep run?

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Gentlemen’s: Grigor Dimitrov — The world No. 11 went out in the first round of Roland Garros but figures to stick around longer at Wimbledon. He won at Queen’s Club and has a favorable draw until a potential quarterfinal clash with his buddy Andy Murray. Playing against the reigning champion and great British hope is a house money match for Dimitrov.

Ladies’: Young American women — Who says American tennis is dead? Sloane Stephens has a draw that could continue her Grand Slam dominance. Taylor Townsend drew a seed in round one, but the seed who’s most lightly regarded, Klara Koukalova. Madison Keys, who will play in her first WTA final on Saturday, drew a tough first-round match in 20-year-old Puerto Rican up-and-comer Monica Puig. If she gets past her, the 19-year-old Keys faces the winner of Townsend/Koukalova. And though Venus Williams, who just turned 34, is one of the oldest players in the field, we consider her young at heart. If she had one more deep run at Wimbledon in her, now’s the time.

7. What are the two popcorn matches of the first round?

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The best first-round matches are the ones you don’t expect. No one sees Darcis over Nadal or Stakhovsky over Federer coming. But that doesn’t mean there aren’t some first-rounders you can look forward to.

Gentlemen’s: Marcos Baghdatis vs. Dustin Brown — Brown is at a career high of No. 78 coming off his win over Nadal in Halle. Baghdatis is the one-time Australian Open finalist who’s had some lean years on tour, but is always exciting. Showman vs. Showman. Put them on a show court, Wimbledon.

Ladies’: Eugenie Bouchard vs. Daniela Hantuchova — Oof, before she’d face Serena, Bouchard will have to get past last year’s U.S. Open quarterfinalist, who’s ranked No. 35 in the world. Of the 96 unseeded women in the draw, only two have a higher ranking than Hantuchova.

8. What’s the best part of Wimbledon?

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You mean besides the classy referencing of the men’s and women’s draws as gentlemen’s and ladies’? And the lush, green grass and the early-morning matches in the United States? And the strawberries and cream and the Pimms to wash it down? And the presence of royalty and/or Pippa Middleton? Those are all great, but I enjoy the ability to use the British spelling of words in posts. Case in point, my neighbour heard a rumour there’s a new coloured racquet being favoured by the gentlemen’s finalist.

9. Okay, are you going to quit stalling and make any predictions?

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Predictions are a fool’s game. No one knows anything, which is how you end up with Marion Bartoli defeating Sabine Lisicki for the 2013 Wimbledon title. But with history as a guide, we can figure on these certainties: 1) At the very least, two of the men’s Big Four will reach the semifinals. 2) There will be at least one surprise in the women’s semifinals. 3) Many people may pick against Serena Williams, but if they had to wager every dollar and possession they had, everyone would choose her to win. With that being said, the official FTW picks for Wimbledon 2014:

What can I say, I play the favorites. Though I hyped Sharapova’s chances above, I think we’ll be deprived of the Serena-Masha quarterfinal, just like we were at Roland Garros. Serena with something to prove is the best Serena. Given her early exit last year and her disappointments in Melbourne and Paris, she fits the bill at the All England Club. On the other side, Makarova is the wild card coming out of the Aga Radwanska quarter. Stephens is 21-6 in her last six Grand Slams. The only thing missing from her resume is a final. Can she get there? If Lisicki and Bartoli can, why not? Anyway, the idea of an All-American final on the day after July 4th is too good to imagine.

Dimitrov in the semifinals over Murray? Call it a hunch, but I think Andy’s Wimbledon hangover continues until the U.S. Open. As for the winner, if I had to do the “every possession” wager, Djokovic is the pick. But I think Federer has one more Slam in him and this looks like prime pickings. Nadal is no sure thing to reach the semifinals. Given Djokovic’s struggles in big matches of late, Federer’s good record against him and a nagging wrist injury, a final would be only slightly in Novak’s favor. That’s why I think Federer gets it done and brings home Wimbledon No. 8. But if you predict he’ll lose to Gilles Mueller in the second round, I wouldn’t call you crazy.

Can Federer win? Will Serena break her slump? The 9 biggest questions for Wimbledon 2014

Tackling all the questions prior to the year’s most anticipated tennis tournament.

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